When I got in to the hobby, it was easy to choose. Each manufacturer had a three tier line up (with variations in each level). Take Shure as an example. Top tier was the V-15. Then the M91 mid-range. Finally, the M44 at the lower end.
Sometimes all you needed to do was upgrade the diamond. Ortofon had the OM, which was available as the ball point pen Pro S; the 10, 20, 30, and 40. All the same except stylus shape. So it was easy to upgrade, and you could reasonably expect some practical improvement between a lower level 10 and a higher end 40.
Again, the Japanese MC scene changed all that. Now, who knows what the differences are? Look at the Koetsu line. 15 cartridges, all wrapped in a different exotic wood or semi-precious stone. I'm sure someone knows, but I have no idea about the difference between, say, a Jade Platinum or an Onyx Platinum model. But at those prices, I guess you'll want one of each. LOL